Potassium Carbonate → HCID 22871860, compound

HRID 53476Notes

Reaction equation

HRID 53476 reaction equation
[P:1]([O:13][CH2:14][C@H:15]1[O:19][C@@H:18]([N:20]2[C:29]3[N:28]=[CH:27][N:26]=[C:24]([NH2:25])[C:23]=3[N:22]=[CH:21]2)[C@H:17]([OH:30])[C@@H:16]1[NH2:31])([O:4][P:5]([O:8][P:9]([OH:12])([OH:11])=[O:10])([OH:7])=[O:6])(=[O:3])[OH:2].C(=O)([O-])[O-].[K+].[K+].[C:38](ON1C(=O)CC(S(O)(=O)=O)C1=O)(=[O:40])[CH3:39].[Na]>O.CS(C)=O>[P:1]([O:13][CH2:14][C@H:15]1[O:19][C@@H:18]([N:20]2[C:29]3[N:28]=[CH:27][N:26]=[C:24]([NH2:25])[C:23]=3[N:22]=[CH:21]2)[C@H:17]([OH:30])[C@@H:16]1[NH:31][C:38](=[O:40])[CH3:39])([O:4][P:5]([O:8][P:9]([OH:11])([OH:12])=[O:10])([OH:7])=[O:6])(=[O:2])[OH:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22871861Adenosine 5′-(tetrahydrogen triphosphate), 3′-amino-3′-deoxy-HCID 86750699Sodium sulfosuccinimidyl acetate

Product 1

HCID 22871860HCID 22871860, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

3'-Amino-3'-deoxyadenosine 5'-triphosphate (15 mg, 26 mmol) and potassium carbonate (21 mg, 0.13 mmol) were dissolved in 2 ml of water. Sodium sulfosuccinimidyl acetate (36 mg, 0.13 mmol; Pierce Chemical, Rockford, Ill.) in 0.2 ml of dimethylsulfoxide (DMSO) was added at 0° C., and the reaction was allowed to proceed at room temperature for twenty-four hours. The product was purified by repeated injections on HPLC using a Synchropak RP-100 column (1×25 cm) applying a linear gradient of acetonitrile 5-22% TEAA (0.85 %/min, flow rate 3 ml/min, t=8.5 min). The appropriate fractions were collected and lyophilized to dryness. The product was obtained as a triethylammonium salt (8.5 mg, 39 %). UV: lmax =259 nm. High resolution MS for C12H18N6O13P3 : calcd. 547. 0145, found 547.0170 (MH3-).

Workup

  1. waitto proceed at room temperature for twenty-four hours
  2. customThe product was purified
  3. customa linear gradient of acetonitrile 5-22% TEAA (0.85 %/min, flow rate 3 ml/min, t=8.5 min)
  4. customThe appropriate fractions were collected

Sources & evidence

ORD record
ord-23a0691d93ff4812bcfe6703f9b0888a
Source dataset
uspto-grants-1997_04
Patent number
US05620676

Reaction notes

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